Where TDG Guides Hikes in the Berkshires
Looking to explore the best hikes in the Berkshires with a local guide? I offer custom hiking tours across Western Massachusetts, including Lenox, Williamstown, North Adams, Pittsfield, Adams, Great Barrington, and the Mt. Greylock region—even into Southern Vermont. Whether you're visiting for a weekend getaway or live nearby, I’ll help you discover scenic trails, quiet forests, and breathtaking views — all tailored to your pace, your group, and your goals. From relaxed family-friendly loops to summit hikes on Mt. Greylock, let’s go on a hike and make your time in the Berkshires unforgettable.
TDG Can Take you on Amazing Hikes in these Berkshire TOwns
NORTH ADAMS, MA
Home to Mt. Greylock, the highest peak in Massachusetts, North Adams is my hometown and perfect for adventurers looking for either rugged, moderate, or easy hikes—all with breathtaking vistas. We specialize in customizing hikes on Mt. Greylock’s amazing array of trails. And the Appalachian Trail goes right through town! Best town for Berkshires hiking!
ADAMS, MA
In the shadow of mighty Mt. Greylock, Adams is my go-to spot because of Greylock Glen recreation area, with its trails for all abilities. Best spot for summit climbs and beautiful easy valley walks in meadows with summit views or alongside peaceful Peck’s Brook. (Also the home of Susan B. Anthony!)
LENOX, MA
Lenox is such a beautiful town to visit, with amazing attractions like Tanglewood, The Mount, Kripalu, and so many amazing hotels and inns. But there are also a couple great parks for hiking. Kennedy Park is good for easy forest walks with a few views, and Lenox Mountain/Pleasant Valley has a moderate climb with an incredible view!
WILLIAMSTOWN, MA
Classic New England charm, home to Williams College, Williamstown has got the exciting West face of Mt. Greylock, with amazing trails from Haley Farm, and some of the best views in the park from Stoney Brook. On the other side of town you have easygoing Mountain Meadow Preserve, Broad Brook, beautiful Taconic Meadow, and a nice moderate climb to an amazing view with Pine Cobble.
We also hike from Great Barrington, Cheshire, Pittsfield, Lee, Stockbridge, Florida, Clarksburg, and Wilmington VT. Just ask!